His Undoing
by LadyShira
Summary: A mature two shot featuring Itachi and a random OC. If you don't like mature stories, then don't read. This is the only warning. Reviews, please!
1. Chapter 1

He pushed my shirt up, slowly rubbing his hand across my stomach and causing small goosebumps to take over my form. Softly, he made his way towards the binding around my breasts, picking at it for a moment as if contemplating he should really go along with what was bound to happen. What started as simple kissing had lead further than either of us had really imagined. This was the most intimate we've reached so far, and I was anticipating of what could be happening in about thirty minutes or so.

"I need to know for sure this is something you want before I go too far." Itachi mumbled, his voice shaking with nerves.

I could already see his excitement; it strained uncomfortably against his gray pants, almost looking painful. Shifting a few times had cause me to bump into it, something that was totally accidental but apparently pleasureful because his hardness seemed to grow bigger than it had been not even ten minutes ago when everything started to heat up.

"Yes, I want you, Itachi." I replied back softly after a moment of thought. We stared into each other's eyes for a moment, searching for any doubts.

"Alright," he finally said, "I'll be as gentle as possible." Even though he's seen me many times with just my breast binding on, he took a moment to stare at the nonexistent cleavage as if it were something worth ogling, then pulled me up gently to slowly unwind the cover up. Once my breasts were free, my nipples reacted immediately, puckering up and screwing into hard little nubs. Embarrassed, I lifted my arm to cover myself. I never really did have much confidence nor much appreciation for the size of my breasts- which were more on the small side than what I would've liked.

Itachi took my arm and moved it away, giving him a complete view of my naked chest. When I finally decided to stare at him, my heart skipped a beat at the flush building up across his face and down his neck. He was staring intently at my breasts with an almost amazed expression.

"Don't stare so much." I muttered, my own face heating up. His gaze immediately switched to stare into my eyes.

"You're beautiful, there's nothing to be ashamed about." He reassured, leaning down swiftly and kissing between the valley of my breasts. He kissed softly to the left, getting closer and closer to reaching my nipple until finally he paused over top of it. His eyes wondered to mine, and slowly, with an intense stare, slid his tongue out and gently traced it. My tense body relaxed at the feeling, a soft sigh escaping my lips.

I leaned back on to the bed, Itachi following suit so his tongue would continue to roam freely on the hard nipple. After a couple of seconds of him slithering his wet appendage around, he wrapped his lips around the nub and gave a gentle suck. A quiet moan spilled out of me, and I threw my head back at the unfamiliar feeling. His hand glided up to my right breast, massaging and running his thumb across the hard little pebble. A shuttered sound escaped me, and I subconsciously reached my hand up and placed it into Itachi's hair, keeping him in place. My movement was futile as he moved to my other breast, giving it the same treatment as he did the left one.

Once he finished, he moved his lips down my stomach, kissing a gentle line downwards to my belly button. He leaned up and grabbed a hold of my panties.

"Is this alright?" He asked, pulling them slightly down. I nodded my head and watched him. He had little help from me, and once they were off, I closed my legs in nervousness.

What if he thinks it's ugly? Or nasty?

Itachi grabbed my knees and parted them, placing them on either side of his body. I closed my eyes tightly, embarrassment leaking into my cheeks again. I felt him move, and then a soft feeling touching around. I jerked as he skimmed over my clit, a noise vibrating in his chest at my reaction. He lightly touched it again, and I jerked once more, a high pitch moan escaping from within. I slammed my hand down on my mouth soon after, appalled by my lack of control over my vocal cords.

"Don't hold back your noises. I want to hear it all." Itachi commanded, taking his thumb and going straight to work, circling and gently moving the sensitive bundle of nerves back and forth. The entire time whimpers were heard, but apparently not loud enough since he circled around it slightly more aggressively. A loud moan made its way up my throat, and Itachi made a small noise himself. He slowly traced down my lower region until he reached my opening. Looking back at me, he took his hand and brought it to my mouth, poking his middle and point finger against my lips.

"Suck." He stated, watching as I drew in his fingers and gently did as he said. I rubbed my tongue around, building up enough spit to where it leaked out of the corners of my mouth and down the bottom of his hand, and pretty soon, he ripped his hand away. Spreading my legs further apart, he placed a wet digit at my hole, and slowly started to push it in. I flinched at the unfamiliar sensation, finding it not uncomfortable, but also not particularly pleasurable. A few gentle thrusts later, I spread my legs as far as they could go, gasping in delight.

The feeling was something I've never felt before; intense and powerful- even if it just was a finger. I could only imagine how true intercourse felt.

He slowly removed his finger and traced it back up to the top, once again circling around the sensitive nub. I turned my head to lay my cheek against the soft bed, my hands clenching until they were fisted tightly into the sheet. I felt Itachi's stare but paid it no mind, too entranced by the way his fingers were making me feel.

"Do you like that?" Itachi whispered sensually but also curiously. I felt my face slowly get red at the crude question, but I couldn't help but let out a small "yes". He moved a bit faster, dipping down in my hole and then coming back up, spreading around the juices escaping me. I felt a tightening in my lower stomach, and almost immediately grabbed Itachi's hand.

"W-Wait.." I stuttered, "I'm starting to feel weird." Itachi removed my hand and continued what he was doing, ignoring my remark and causing the same feeling to intensify. I whimpered in pleasure as his finger slid back inside me. His unoccupied hand slid up my stomach and started to toy with my breasts, switching between the two and softly pinching my nipples. I groaned aloud, my legs shaking slightly as the feeling became more powerful. Itachi added another finger, slowing down enough so I could get used to the new accommodation. The uncomfortable feeling didn't last long as he started to pick up the pace again, twisting his hand and bending his fingers.

The ball clenching in my stomach began to be too much, and like a dam, it all released. A sharp moan was heard as I twisted my body around Itachi's hand, his fingers still moving deep inside me and hitting a spot, making the pleasure become stronger. My shaking worsened, causing Itachi to put weight on me to keep my frame from bucking wildly.

"Itachi!" I screamed, grabbing at his hand still moving. He pumped a few more times and then stopped, feeling the way my muscles spasmed around his fingers. My body continued to shake until the intense pleasure reached its end.

I slumped back and panted, my heart beating wildly in my chest. Itachi took his fingers out, and I could faintly feel drops of my essence running down my skin and onto the bed. I watched Itachi as he examined his fingers, and then casually popped them into his mouth. He stared into my wide, shocked eyes, slowly removing his fingers with an audible suctioning sound once he was done, and crawled closer to me.

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 **Revised 1/18/2017 No major changes were made.**


	2. Chapter 2

"Did you like that?" He asked genuinely, kissing me roughly right after. It was sloppy and wet, but yet quite satisfying in my exhausted state.

"Mhmm." I hummed, running my hand up his back softly.

"Do you want to go further?" He whispered in my ear, nibbling gently on the lobe. I moaned quietly, nodding as my arousal started to increase again.

We both sat up to rid Itachi of his burden clothes. Once I finished undoing the buttons on his pants, I took a hold of them and gently pulled them down over his erection. The front of his boxers had a small wet mark at the end of the bulge, causing me to blush furiously. He kicked his pants the rest of the way off and grabbed his boxers to do the same. In my bout of embarrassment, I looked away as soon as he removed the undergarment.

He grabbed my thighs, running his thumb gently across my skin, and then pulled me to the edge of the bed. I let out a silent gasp of surprise, and then another when I caught sight of his hard manhood.

The base was surrounded by a dark mass of course hair; veins ran up the length of his shaft, some small and some bulging, and led to a mushroom shaped head that glistened some with wetness.

I looked away in nervousness, wondering how exactly it was suppose to fit inside of me.

"I'll be gentle, I promise." Itachi spoke, pulling me even closer. He took his hardness in his hand and ran the wetness from his tip down the entire length, then softly ran it up and down my slit. I leaned my head back into the mattress, closing my eyes at the blissful feeling. He did it a few more times, each forcing a whimper out of me as it brushed against my clit.

Itachi stopped at my entrance, pushing gently at the available opening. He applied some force, allowing the head of his member to pop inside.

"Don't be so tense." He mumbled, stroking above my mons affectionately. I tried to listen, relaxing whatever muscles I could in my body. He thrust softly, sliding deeper inside until he came to a stop. He grabbed my hand and soon after tore through my virgin barrier; a quiet whine of pain left my mouth, the burning sensation being something I didn't anticipate hurting so much. Itachi held still, locking our hands tightly together and allowing the pain to dissipate into nothing. After a bit, he hesitantly pulled out and pushed back in. A quiet moan drawled out from deep within his chest, and after a few moments, from me as well.

Itachi made love to me soft and sweet, keeping his promise about being gentle. It wasn't long after we started that the familiar feeling of release came upon me, licking feverishly to be let loose. I groaned out, raking my fingernails across his back in pure pleasure, causing him to speed up.

Lewd noises filled the air, from our panting moans to the sound of our flesh meeting between each thrust Itachi made.

"Oh, Itachi!" I yelled, grasping his forearms, "please, don't stop. Harder, harder!"

He complied immediately, increasing the pace and the strength which drew from it. His heavy breathing could be heard amongst my cries of ecstasy, adding onto the release that was just about to bubble over.

It wasn't long before he hit a certain spot in me, the same one from earlier, causing my moans to sputter in delight as the thrusts he gave were nonstop. A few more delicate hits had me seeing white, exploding in pure euphoria as my body writhed and shook in intense pleasure. Itachi continued on, grunting every now and then as he was nearing his own release. A few seconds later, he slammed as far as he could in me, spilling his seed. The warm spurts hit deep inside, each one in a different spot. Once the spurts slowed, he gave fast little pumps of his hips, making sure that he completely drained himself.

After he finished, he still gave small thrusts as we both tried to catch our breath, then came to a complete stop as our gazes met. We stared into each other's eyes as he removed himself, and I gasped in wonder at the feeling of his essence running out of me and on to the bed.

"I love you." He said, running the back of his hand across my red stained cheek.

"And I love you."

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 **Well, you guys, I hope you enjoyed this. This was my first time at any type of mature scene, and I gotta say... I'm a little red in the face at where my imagination can go haha. Sorry if there are any grammatical errors, and if you could be so kind, please leave a review and tell me what you think. It would mean a whole bunch!**

 **Revised 1/18/2017 No major changes were made.**


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